2-Hydroxyestradiol (CHEM008140)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:39:14 UTC
Update Date2016-11-09 01:13:44 UTC
Accession NumberCHEM008140
Identification
Common Name2-Hydroxyestradiol
ClassSmall Molecule
DescriptionA 2-hydroxy steroid that consists of 17beta-estradiol having an additional hydroxy group at position 2.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • My Exposome Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(17beta)-Estra-1,3,5(10)-triene-2,3,17-triolChEBI
2-Hydroxyestradiol-17betaChEBI
2-OH-e2ChEBI
2-OH-EstradiolChEBI
(17b)-Estra-1,3,5(10)-triene-2,3,17-triolGenerator
(17Β)-estra-1,3,5(10)-triene-2,3,17-triolGenerator
2-Hydroxyestradiol-17bGenerator
2-Hydroxyestradiol-17βGenerator
(17b)-Estra-1,3, 5(10)-triene-2,3,17-triolHMDB
(17beta)- Estra-1,3, 5 (10)-triene-2,3,17-triolHMDB
1,3,5(10)-Estratriene-2,3,17Beta-triolHMDB
17beta-2-HydroxyestradiolHMDB
2,3,17b-Trihydroxyestra-1,3,5(10)-trieneHMDB
2-Hydroxy-17beta-estradiolHMDB
2-Hydroxy-estradiolHMDB
ECSHMDB
Estra-1,3,5 (10)-triene-2,3,17.beta.-triolHMDB
Estra-1,3,5(10)-triene-2,3,17-beta-triolHMDB
Estra-1,3,5(10)-triene-2,3,17-triol (acd/name 4.0)HMDB
Estra-1,3,5(10)-triene-2,3,17b-triolHMDB
Estra-1,3,5(10)-triene-2,3,17beta-triolHMDB
2-Hydroxyestradiol-17 alphaHMDB
2-Hydroxyestradiol-17 betaHMDB
2-Hydroxyestradiol, (17alpha)-isomerHMDB
2-Hydroxyestradiol, 4-(14)C-labeledHMDB
Chemical FormulaC18H24O3
Average Molecular Mass288.381 g/mol
Monoisotopic Mass288.173 g/mol
CAS Registry Number362-05-0
IUPAC Name(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-4,5,14-triol
Traditional Name(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-4,5,14-triol
SMILES[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C(O)=C3
InChI IdentifierInChI=1S/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1
InChI KeyDILDHNKDVHLEQB-XSSYPUMDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 3-hydroxysteroid
  • 2-hydroxysteroid
  • Hydroxysteroid
  • 17-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Polyol
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.051 g/LALOGPS
logP3.39ALOGPS
logP3.44ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.67ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity81.89 m³·mol⁻¹ChemAxon
Polarizability33.08 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adr-2490000000-7e8a9e3990faceb5f6d0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-002u-1002900000-79ac7707883246949511Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00ei-2950000000-326e2d3fee4fb8b3ca6cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-2910000000-553a7988f4c2019ec5d5Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0f96-8975000000-eef1fcf44ed6a27f53a9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0190000000-0e1c17e32d9c1e4063ebSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-0790000000-01416dcd9eea3747d3c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-6970000000-d27a7add654c423ec534Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-805faf5743eec20547cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-c39e06f8fdeeb111e97fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-1190000000-36538cb7b1a03d7b2ff7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-572916cfebc6538c52d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01w0-0490000000-7a41b9ec75d4c7c28c73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-3910000000-4dd2fe1697c6e685073eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-843a74fabb1d0eb512a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-40c60966bb1ce4624953Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-1009-0090000000-1c821729dedb3f0fecbeSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB07706
HMDB IDHMDB0000338
FooDB IDFDB021962
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5327
PDB IDNot Available
Wikipedia Link2-Hydroxyestradiol
Chemspider ID216475
ChEBI ID28744
PubChem Compound ID247304
Kegg Compound IDC05301
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11812141
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=14563383
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=14872091
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15662657
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=16404153
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16421288
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=16788039
8. Kiuru, Paula S.; Wahala, Kristiina. Short synthesis of 2-methoxyestradiol and 2-hydroxyestradiol. Steroids (2003), 68(4), 373-375.
9. Takanashi K, Honma T, Kashiwagi T, Honjo H, Yoshizawa I: Detection and measurement of urinary 2-hydroxyestradiol 17-sulfate, a potential placental antioxidant during pregnancy. Clin Chem. 2000 Mar;46(3):373-8.
10. Elce JS, Bird CE, Chandra J: Water-soluble products of the estrogens. Bile metabolites of 2-hydroxyestradiol-17beta in man. J Clin Endocrinol Metab. 1973 May;36(5):1027-30.
11. Zhu BT, Conney AH: Functional role of estrogen metabolism in target cells: review and perspectives. Carcinogenesis. 1998 Jan;19(1):1-27.
12. Kuiper GG, Carlsson B, Grandien K, Enmark E, Haggblad J, Nilsson S, Gustafsson JA: Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology. 1997 Mar;138(3):863-70.
13. Schaeffer JM, Hsueh AJ: 2-Hydroxyestradiol interaction with dopamine receptor binding in rat anterior pituitary. J Biol Chem. 1979 Jul 10;254(13):5606-8.